Date: Sat, 30 Aug 2008 13:28:47 -0700 (PDT)
From: texanasianlover (at) yahoo (dot) com
Subject: Jack & Jill Meet - TG First Time
Jack and Jill Meet
texanasianlover [at] yahoo
It was when I went to the patio to enjoy a cigar after dinner that we met.
On the road for business, I found a decent bar and grill near my hotel
where I was welcome to enjoy a fine smoke. I had dinner and then moved
outside for a relaxing smoke in the cool weather. I lighted a
Churchill-sized stick and after a few minutes of solitude, an exotic
looking brunette spoke from just behind and to the side of me.
"I love the smell of a fine cigar," she said in a sultry voice that got my
attention.
I turned to look as she moved forward into my view and was pleased to see a
young woman dressed in a red formfitting top with a leather mid-thigh
skirt, and more importantly, luxurious long dark hair as straight as if
ironed.
"You're welcome to enjoy one for yourself if you wish," I said while
politely standing to greet her. "I'm Jack,' I added as I extended my hand
to take hers lightly.
"Jill," she said with a smile and laugh.
"No kidding, Jack and Jill?" I questioned.
We both had a short laugh and I motioned for her to sit across from
me. When she sat down I got a great look at a long pair of tan legs and was
impressed with the slight curve of her hips, slender torso, and just right
sized breasts.
Now I was looking at her, face level with mine, and saw her dark eyes and
lusciously thick lashes. She was exotic in that she was part Asian,
possibly part Anglo and almost had a look of a Latina as well.
It is quite sexy to when a hot chick smokes a large sized cigar. Clearly
it's the oral phallus action but, there is also a sexy confidence to such a
woman that I find attractive.
Jill allowed me to light the cigar as she expertly turned it, keeping it
far off of the flame demonstrating that she was not new to the delights of
a fine cigar. I was already hoping she was not new to other oral delights
as well!
We visited for some time and she was obviously inserting and removing her
cigar in as sexy a manner as you could imagine. It would have taken nothing
more than her walking up to me to get me excited and thinking about sex
with her. Add the sexy smoking, with the good conversation, and this became
a pursuit I could not refuse.
After I thought I'd enjoyed about as much as I could take, Jill began
blowing smoke rings! Wow! Putting her full lips in that rounded, puckered
position needed to blow the rings was more than suggestive, it was almost
pornographic.
By this time she knew I was staying in the hotel next door and much about
where I was from and what I did for work. I had tried to get her to talk
more about herself but she would say little except that she worked in show
business.
One thing that I kept wondering about was if at some moment she was going
to tell me she was for hire. It's not unusual to have attractive women
strike up conversations when smoking a cigar â€" you get everything from
how the smell reminds them of their fathers to how they enjoy smoking too,
as if it is the greatest novelty in the world. But few are as sexually
suggestive as was Jill.
I'd already eaten dinner so it wasn't a great idea to ask Jill to
dine. Instead I decided to blurt out: "Jill, how about spending the rest of
the evening with me at my hotel?"
"I can tell you're `up' for it," she replied confidently while glancing
through the metal screened tabletop toward my crotch and smiling.
"Let's go," I said as I stood up and offered her my hand.
While taking my hand and pulling herself up, Jill said: "Jack, I don't want
you to get the wrong idea. I spoke to you because I was looking for company
in enjoying a cigar. But after talking with you I felt a real spark," she
said. "I'm not a slut and don't go around meeting guys and going off with
them as a regular behavior. In fact, it's really tough for me to meet and
spend time with most men."
"I can't imagine that, as gorgeous as you are. Plus you are a great
conversationalist," I replied.
"I'm a bit different," she said as she pressed my hand and stopped walking
for a moment. "I don't have any medical problems or anything but, I have a
situation that can sometimes be a bit of an embarrassment."
I pulled her hand and started us walking across the parking area toward my
hotel again.
"I'm sure I can deal with it Jill, whatever it is," I said confidently
while pulling her along.
"Just be gentle with me, please," Jill said in a pleading sort of manner as
we walked.
"I promise," I told her, meaning it.
---
We had held hands up the elevator and down the hallway to my room. Our body
heat and flushing cheeks that told the entire story of our attraction.
After we entered my mini-suite and walked just as far as the small couch, I
felt Jill's hand on my ass and we turned into a passionate kiss. Our
tongues lashed as each other and we were filled with the exhilaration of
hot lust being fueled by tasting the first morsels of what would become a
banquet of sex.
As we groped and rubbed our bodies together and began to explore with our
hands, we fell lightly to the sofa without parting our mouths. I was
enchanted with Jill's olive, smooth skin and sensual looks and even more
delighted to find her wearing high quality, lacy lingerie under her blouse.
Her small breasts were swollen and encased in a front-clasp bra through
which her hard nipples could be seen as they pressed hard against the
feminine fabric. I had much practice with this type of fastener and easily
liberated her breasts in one quick, one-handed move.
As I kissed my way down her slender neck, Jill was moaning and breathing
harder. When I brushed my hot tongue across her nipples, her back arched
and she pressed her chest toward my mouth for more.
While I bathed her nipples with my tongue my hands began working around to
her hips and lower back. I began to unbutton and unzip her leather skirt
and she assisted by moving in just the right way.
"Jack," she said breathlessly. "Please promise me again that you'll be
gentle."
It sounded as if she was imploring me not to hurt her making me think that
possible she could be a virgin. I didn't mind and it wouldn't be my first
time but, I found it hard to believe given our ages and her overall sexual
confidence.
While nibbling on her breasts and stomach, I pulled her skirt down as she
lifted herself to allow it to pass. She pulled the one leg up and through
it that was hanging over the edge giving me full access to her body.
Again, her panties were of the highest quality and very feminine, something
that is important to me and adds greatly to my enjoyment.
I began kissing my way down to her pussy and when my mouth began to press
against the fabric where her wet slit and clit should be, I felt heat but
not the expected wetness and musk.
Moving back just slightly so that I could see the area more clearly, I was
more than surprised to see what seemed to be a smallish, maybe five inch,
cock pulled back between her lovely thighs.
In my surprise, I looked up at her gorgeous face and saw the most beautiful
but fearful expression. Again, before I could speak, she said: "Please,
please be gentle with me."
I was no stranger to what a shemale or transsexual was. I had fantasized
about being with one before and looked at pictures and movies online. But
I'd never acted on such a desire nor had it been a major interest.
At that moment, while looking at her lovely expression, I made a
decision. I directed my gaze back toward her boy clit, pulled the crotch of
the panties back so that there was more room, reached in and moved her cock
up and forward, and then began kissing it as if it were the most sensual
clitoris I'd every touched.
As I did this, Jill relaxed and began running her fingers through my hair
and pulling me closer to her boy clit. As she did, I moved the panties to
the side and did something I thought I'd likely never do. I took a cock
into my mouth and smothered it with saliva while running my tongue around
and around its full width.
"Oh, Jack. It feels so wonderful," she began to say repeatedly as she
pressed my head lightly.
I just sucked and sucked, moving my head up and down and working my tongue
over the sensitive areas of her boy clit. As she began to lift her hips up
thrusting her cockette into my mouth, I slid my hands under her ass and
squeezed in rhythm.
It wasn't long before she began to tremble and I felt what was
coming. Another decision to reach and I chose to keep her in my mouth
through full orgasm.
Her thrusting stopped with her hips pressing up against me and the pressure
from her hands on my head become stronger. Then her clitty erupted in my
mouth. Hot spurt, after hot spurt filled my oral cavity while she held me
in place.
Soon Jill relaxed back down pulling her clit from inside my mouth. She then
began pulling my head up to hers and kissing me, taking her own spunk from
my mouth and swallowing it. Wow! That was sexy. I didn't mind taking in my
mouth but I wasn't up to swallowing on this my first time. Her action
relaxed me and we then kissed slowly as we enjoyed the feeling of the
natural lubricant on our lips and in our mouths.
During this time, Jill's hands had found their way to my crotch, unzipped
my trousers, and had started to fondle my hard, wet cock.
Suddenly she pushed me back, crawled to the floor, and planted herself on
her knees right in front of me. As she locked on my eyes with her dark
oriental eyes, she lowered her mouth onto my cock and began giving me the
most intense blowjob I'd ever experienced.
Just like Jill, it did not take long before I gushed into her mouth. And,
unlike me, she swallowed it all as if she loved it.
She didn't get up to kiss this time though. Jill stayed between my legs and
licked my cock gently, careful not to over stimulate but directly enough
keep it from going completely soft.
I just looked at this lovely woman between my legs and did everything I
could to burn this sexy image into my memory to last a lifetime. She was
more beautiful, feminine and sexy than ninety percent of the women I'd ever
met, much less those I'd made love with. And, she was making love to my
cock and my balls in a way that no other woman had ever come close to.
"That was incredible," I said to Jill as she was licking my balls and
working me back to full tumescence. "And what you're doing now feels like
heaven."
"Mmmm", she said looking at me while taking my cock back in her mouth and
deep throating me.
It was a new and fantastic experience to feel my cock enter the top of her
throat; I could feel the vibrations in my cock head when she moaned.
After a few more minutes of getting me back to life, Jill came back up on
the couch and began licking and kissing my ear and neck.
"Jack, I want to feel you inside me," she whispered in my ear between
nibbles. "I want your big cock in my ass."
As she was saying this and nibbling on my ear, her hand was gripping my
cock strongly keeping it at full attention.
"I'd love to fuck your lovely pussy," I said and began to pivot my body so
that I could stand.
I stood and removed the rest of my clothes with Jill's help and we moved to
the bed which had already been turned down by housekeeping.
On the way, Jill had grabbed some KY from her purse and I began to apply it
to her very sexy, smooth, boy pussy.
After some time of lubing her and my cock, she rolled onto her back and
pulled her legs high in the air giving me full access. I placed two pillows
under her lower back and then moved in on my knees with my cock pointed
straight toward her boy pussy.
"Please Jack, please fuck me," she said with anticipation. "Put your manly
cock in my pussy-ass."
"Jill, I'm going to fuck you with my hard cock sweetheart," I said as I
pressed it against her relaxed opening.
Looking down at her lovely breasts, gorgeous face, and long dark hair
fanned out on the bed, I couldn't believe that she had a cock and no other
sign of masculinity. No Adam's apple, no think torso or arms, just all
feminine woman with a very smooth and nice looking cock.
"Fuck me Jack," she said as a command.
I pushed into her ready ass and entered her sensual body. Deeper and deeper
I pushed, slowly and deliberately as her eyes rolled back and closed while
her lips parted and mouth gaped open at the sensation.
I held her legs tightly against me with her ankles on my shoulders. Then I
began a slow in and out thrusting rhythm that grew and grew until I was
fucking her with full vigor and speed.
"That it, Jack. Don't stop. Fuck me, fuck me, Jack," she said with
repetition.
"I'm fucking you Jill," I said as I moved faster and harder into her ass
holding her legs ever tighter. "I'm fucking you, you beautiful girl. Feel
my cock pulsing in your tight pussy. Feel it!"
I began to order her to enjoy the fucking she was getting and the more I
talked the more she thrashed around on the bed. One hand was pinching her
nipples and the other was thrown up and behind her grasping the headboard
railing.
"Jill, I'm going to shoot into you!" I exclaimed.
"Yes, yes," she panted. "Shoot your come in my pussy. Please, shoot it deep
inside me."
"I'm going to fill you with my come," I said loudly just as I began to
seize. I plunged as deep as possible and enjoyed the massive orgasm as my
both my muscles and hers pulsated. The feeling of her tight hole gripping
and pulsating on my cock intensified the orgasm beyond belief.
Soon we both began to relax and Jill's legs lowered to the bed as I pulled
out of her tight ass.
I crawled up beside her and kissed her as I stroked her now very hard
cockette with my hand.
"You are so incredible," I told her. "Let me take your come again."
She nodded yes and I moved my mouth to her cock and began, for the second
time ever, sucking a penis. But this was no hairy boy dick; this was a
feminine, smooth, attractive large clit. And I sucked her and squeezed her
small balls until she again shot her load into my mouth. This time, I
swallowed her seed.
Jill and I took a long shower together after that, slept for a while, and
made love again a few hours later. This time, I told her of my love of ass
play and stimulation and asked her if she would be willing to fuck me.
"Jack, I'd love to fuck you," she said excitedly. "I'd love to fuck you
more than anything I've ever done in my life."
Jill rimmed my ass with her tongue, which was a tremendous feeling, then
lubed me up good. And, since I often use a small dildo on myself when
alone, I was ready to accept her thin cockette immediately.
"Get on all fours, baby," she said.
When I did, Jill came behind me and pressed the head of her cock against me
and the feeling was indescribable. The feeling of her cock was much better
than from a plastic phallus. As she pushed into me, what I noticed most was
the heat.
"Oh baby," I said with my head buried in a pillow and my ass sticking up in
the air taking her cock. "It feels so good."
Slowly Jill began to fuck me, a feeling I had never been able to attain
while just holding a dildo in my ass. It was fantastic as she slid in and
out. I could feel sensations I had never before noticed.
"Jack, your ass is mine," she said playfully as she began to fuck me faster
and harder.
"Yeah, baby," I replied. "Fuck me hard. Make me your plaything."
Her cockette moved in and out of me faster and faster and when she reached
around and grabbed my swollen cock, I thought I would explode from
pleasure. But, before I exploded Jill shouted: "Here it comes baby, here
comes my pussy juice!"
And with that, she shot a hot load deep into my bowels. The feeling of the
hot liquid entering me was unmatched by anything I'd ever felt. And just as
she came, she squeezed my cock causing to erupt for a third time. As I shot
my load, each spasm clamped down on her cockette in my ass and milked every
bit of her sweet juice from her boy clitty.
After our bodies relaxed, we lay next to each other and kissed and stroked
each other for a long period of time.
Finally, I asked: "Sweetheart, you never have told me what you do except
that you are in show business, what kind of show business?"
"I bet you think I must be a stripper or something," Jill said
coyly. "Well, I'm not. I own the local art house movie theater. And what's
more, there's not a person in this town that knows my little secret â€"
except you."
"Well Jill, if you don't mind," I said, "I'd like to keep it that way but
with one condition."
"What's that?" she asked.
"That they all do get to know that I'm your man," I answered.
She just smiled and kissed me deeply and lovingly.
"I think we might arrange that," she said.